The present invention relates to the production of C.sub.1 to C.sub.5 alkyl nitrites and most particularly to an improved method for the production of isopropyl nitrite. Isopropyl nitrite is known per se and finds use as an intermediate in the production of the biocide Paraclox which is alpha-chloro-alpha-oximino-4-hydroxyacetophenone. This latter compound has the structural formula ##STR1## The preparation of this compound has been described by N. Levin and W. H. Hartong, Journal of Organic Chemistry, (1942), 7,408. Preparation proceeds by reacting hydroxyphenacyl chloride with isopropyl nitrite in the presence of hydrogen chloride to yield the product. The reaction can be depicted by: ##STR2## Alpha-chloro-alpha-oximino-4-hydroxyacetophenone is known to have good antibacterial and germicidal properties. Thus, the compound has found use as an industrial biocide to control the growth of bacteria and microorganisms which develop in water-based media used in the manufacture of various industrial products. Its antibacterial and germicidal properties are more fully described in U.K. Pat. No. 1,290,646.
The preparation of isopropyl nitrite is known in the art. Organic Synthesis Coll. Vol 3, 191 (1955) at pages 26-27 teaches the formation of a water, isopropanol, sulfuric acid mixture which is then added to an aqueous sodium nitrite solution. A problem with this method is the formation of a three phase reaction product including solid sodium sulfate in a third phase. In this prior art method, the isopropanol and sulfuric acid are first premixed and then dripped into sodium nitrite. The same problem is noted in the production of n-butyl nitrite at Organic Syntheses Coll. Vol 2, 108 (1943) at page 108. It has now been found that C.sub.1 to C.sub.5 alkyl nitrites may be prepared by a one step reaction of a C.sub.1 to C.sub.5 alkyl alcohol, an alkali metal nitrite and a hydrohalic acid in aqueous media. In the most preferred embodiment one may produce isopropyl nitrite by reacting isopropanol with sodium nitrite and hydrochloric acid in water according to the scheme: ##STR3## It has been unexpectedly found that by premixing the isopropanol and sodium nitrite and then adding the hydrochloric acid, that there is a decreased production of the nucleophilic substitution product, such as isopropyl chloride, as an impurity. The result is a two phase reaction product, a lower aqueous phase which is a saturated sodium chloride solution and an upper organic phase of isopropyl nitrite. These phases are then separated easily.